Reimagining Rock Planning- How ChatGPT Elevates EOS Execution with SMART Rocks and Milestones

As an EOSÒ Integrator with 14+ years of

continual experience using the EOSÒ platform or framework, I have led countless EOSÒ Quarterly Planning Sessions across many entrepreneurial companies. Time and again, the most transformative (and exhausting) part of the day is when the leadership team aligns on its top priorities: SMART Rocks. These 6– 8 short-term goals are the backbone of establishing and driving traction in the business in a 13-week quarter. But for all the clarity SMART Rocks & executable plans with milestones provide once finalized, the process of crafting them can be arduous.

The Traditional EOSÒ Rock Planning Process

In a typical EOSÒ Quarterly Session, teams start with a brainstorm: What are the 6–8 most

important things we must accomplish this quarter? Each potential Rock goes through scrutiny— does it support the 1-Year Plan? The 3-Year Picture? The Vision? Then begins the real work: converting ideas into SMART Rocks (Specific, Measurable, Achievable, Relevant, Time-bound), followed by writing six supporting milestones to be executed bi-weekly across the 13-week quarter.

Using ChatGPT for Rock and Milestone Planning

Now re-imagine the same process—but it takes upwards to 60 minutes total instead of 2.5 hours in the planning session plus another 1-3 hours outside of the meeting to tighten-up “SMARTing” the Rocks and creating a 6-milestone plan to execute for the quarter

ChatGPT can take well written, drafted goal and output a SMART-formatted Rock with 6 well structured, time-bound milestones in seconds. The SMART-formatted Rock and the 6

milestones will be of higher quality, more comprehensive, and significantly more robust that

what is generated in the “traditional” process. I have seen this first-hand, and it is game changing! With just one or two well-written prompts based on prompt engineering techniques, leadership teams get clear, consistently drafted Rocks which are often 80%-90% of the way to final completion with little to no editing. This leaves extra time to assess resource requirements to be deployed assuming a cross-functional organization and the potential for conflicts in resource needs or timing all of which can be mitigated more effectively. EOSÒ is about simplifying business. ChatGPT is simply a tool to help you do that—faster, clearer, and with

more “traction.”

Top 6 Improvements I Realize When Using ChatGPT

1. 75% Increase in Speed: Instead of spending 3+ hours on Rocks in the EOSÒ Quarterly

Planning session plus additional hours outside of meeting to complete this exercise,

teams can now complete one Rock in ~20 minutes or multiple Rocks in about one hour.

That is a minimum of 6+ hours in time savings across the session. My experience is a

75% increase in speed leaving valuable time that can be spent solving issues, reviewing

the Scorecard, or coaching team members.

2. Increased Quality & Clarity of Rocks: ChatGPT ensures Rocks hit all the SMART

criteria by default. Vague goals like “Get our inventory under control” become clear

targets like “Reduce inventory inaccuracies by 40% by June 30.”

3. Robust & Well-Aligned Milestones: ChatGPT, with the use of solid prompt

engineering will provide nearly complete bi-weekly milestones (6 for a 13-week

quarter)to execute which are clear, comprehensive, & robust.

4. Consistency Of Milestones: Milestones, when created by various individuals, often vary

in depth, structure, and clarity. With ChatGPT, every milestone follows a predictable and

actionable format—making it easier for team members to own and report progress in

Level 10 (L10) Meetings™.

5. Strategic Focus: By accelerating the administrative portion of Rock planning, leadership

teams have more time to zoom out and work “on-the-business”—reflecting on market

changes, customer experience, and operational health. In other words, strategy gets space

to breathe.

6. Team Engagement: Slow planning can be exhausting and drains energy even for the

most energetic strategy enthusiasts. When Rocks come together quickly, effectively with

high quality and clearly, team morale stays high, collaboration improves, and people

leave planning sessions motivated to execute.

Challenges and Cautions

AI and ChatGPT in this user’s experience and example does not replace the leadership team—it supports it. ChatGPT cannot decide what is most important or ensure that Rocks align with your Vision/Traction Organizer™. It does not know your leadership team’s collective capabilities much less that of the individual members, or team members in the organization, your customers, or your constraints. If not prompted correctly via solid prompt engineering, it may return suggestions that sound good but are not truly aligned. The key is using ChatGPT as a draft partner to accelerate towards a near-complete solution or answer, not a decision-maker or final arbitrator! One final cautionary note to be ever mindful of – Do not allow AI, ChatGPT, to dull your leadership team’s thinking. Do not get lazy!

Summary

Integrating ChatGPT into your EOSÒ Quarterly is not a shortcut—it is an upgrade. Rocks

become sharper, milestones clearer, and your planning session regains time and energy. Instead of stalling in the weeds of wording, your leadership team can stay focused on impact. Even with just one AI-assisted Rock, you will without question feel the lift. Multiply that by six or eight

Rocks, and you have a transformative new way to drive an improved and updated EOSÒ

Quarterly Planning Session resulting in a faster start to the 13-week quarter and Rocks when

completed that are truly impactful and resulting in increased momentum and traction in eh

business.

At your next EOSÒ Quarterly, give ChatGPT a seat at the table. Try using it for SMARTing your Rocks and creating accompanying milestones and see how it accelerates your process without sacrificing quality. You will see your leadership team’s engagement rise as ambiguity

disappears. You will wonder how you ever ran the EOSÒ Quarterly and Annual sessions without it.

1 Watch for a follow-on article targeted towards prompt engineering and specific use in this EOSÒ Quarterly Planning Session.